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Physicochemical Properties of Various 2-Hydroxyethylammonium Sulfonate -Based Protic Ionic Liquids and Their Potential Application in Hydrodeoxygenation.

ABSTRACT: In order to obtain the regularities of physicochemical properties of hydroxy protic ionic liquids (PILs) and broaden their potential application, a series of 2-hydroxyethylammonium sulfonate-based PILs were synthesized through proton transfer reaction and characterized by NMR and FT-IR and elemental analysis. Their phase transfer behavior (T _m) and initial decomposition point (T _d) were characterized by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), respectively. Meanwhile, the regularities of density (ρ), viscosity (η) and electrical conductivity (σ) of synthesized PILs at different temperatures were measured. The results indicated that their physicochemical properties were tightly related with their structures and the interactions between cations and anions. In addition, the dissociation constants (pKa) of synthesized PILs were obtained by acid-base titration, which revealed that all synthesized PILs had pKa exceeding 7 and their cations were the crux of determining the pKa value. Moreover, several synthesized PILs with a low melting temperature also showed potential application in the deoxidation reaction of cyclohexanol, as they had conversion rates approximating 100% and the selectivity of cyclohexane or cyclohexene was about 80%.

SUBMITTER: Cai G

PROVIDER: S-EPMC6460099 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Transport properties of protic and aprotic guanidinium ionic liquids.

Project description:Ionic liquids (ILs) are a promising class of solvents, functional fluids and electrolytes that are of high interest for both basic as well as applied research. For further fundamental understanding of ILs and a successful implementation in technical processes, a deeper insight into transport properties and their interrelations is of particular importance. In this contribution we synthesised a series of mostly novel protic and aprotic ILs based on the tetramethylguanidinium (TMG) cation that is a derivative of the superbase guanidine. Different substitution patterns and anions from acids with broadly varied pK a values were investigated. We measured general properties, such as thermal transitions and densities of these ILs, as well as their transport quantities by means of rheology, impedance spectroscopy and NMR diffusometry. Different models for the correlation of the transport properties, namely the Nernst-Einstein, Walden and Stokes-Einstein-Sutherland relations were applied. The deviation from ideal behaviour of fully dissociated electrolytes, often termed as ionicity, was quantified by the reciprocal Haven ratio, fractional Walden rule and ionicity obtained from the Walden plot. Velocity cross-correlation coefficients were calculated to gain further insight into the correlation between ion movements. Both protic and aprotic TMG ILs show transport properties comparable to other ILs with similar molecular weight and high ionicity values especially in contrast to other protic ILs. Lowest ionicity values were found for the protic ILs with smallest ΔpK a values between constituting acid and base. This can either be explained by stronger hydrogen bonding between cation and anion or lower anti-correlations between the oppositely charged ions. These results aim to provide insight into the properties of this interesting cations class and a deeper understanding of the transport properties of ILs and their interrelations in general.

| S-EPMC9091945 | biostudies-literature

Thermal and Electrochemical Properties of Ionic Liquids Bearing Allyl Group with Sulfonate-Based Anions-Application Potential in Epoxy Resin Curing Process.

Project description:Sulfonate-based ionic liquids (ILs) with allyl-containing cations have been previously obtained by us, however, the present study aims to investigate the thermal, electrochemical and curing properties of these ILs. To determine the temperature range in which ionic liquid maintains a liquid state, thermal properties must be examined using Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TGA). Melting, cold crystallization and glass transition temperatures are discussed, as well as decomposition temperatures for imidazolium- and pyridinium-based ionic liquids. The conductivity and electrochemical stability ranges were studied in order to investigate their potential applicability as electrolytes. Finally, the potential of triflate-based ILs as polymerization initiators for epoxy resins was proven.

| S-EPMC9864641 | biostudies-literature

Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO2 Capture.

Project description:Ionic liquids, which are extensively known as low-melting-point salts, have received significant attention as the promising solvent for CO2 capture. This work presents the synthesis, thermophysical properties and the CO2 absorption of a series of ammonium cations coupled with carboxylate anions producing ammonium-based protic ionic liquids (PILs), namely 2-ethylhexylammonium pentanoate ([EHA][C5]), 2-ethylhexylammonium hexanoate ([EHA][C6]), 2-ethylhexylammonium heptanoate ([EHA][C7]), bis-(2-ethylhexyl)ammonium pentanoate ([BEHA][C5]), bis-(2-ethylhexyl)ammonium hexanoate ([BEHA][C6]) and bis-(2-ethylhexyl)ammonium heptanoate ([BEHA][C7]). The chemical structures of the PILs were confirmed by using Nuclear Magnetic Resonance (NMR) spectroscopy while the density (ρ) and the dynamic viscosity (η) of the PILs were determined and analyzed in a range from 293.15K up to 363.15K. The refractive index (nD) was also measured at T = (293.15 to 333.15) K. Thermal analyses conducted via a thermogravimetric analyzer (TGA) and differential scanning calorimeter (DSC) indicated that all PILs have the thermal decomposition temperature, Td of greater than 416K and the presence of glass transition, Tg was detected in each PIL. The CO2 absorption of the PILs was studied up to 29 bar at 298.15 K and the experimental results showed that [BEHA][C7] had the highest CO2 absorption with 0.78 mol at 29 bar. The CO2 absorption values increase in the order of [C5] < [C6] < [C7] anion regardless of the nature of the cation.

| S-EPMC8839255 | biostudies-literature

The Proton Dissociation of Bio-Protic Ionic Liquids: [AAE]X Amino Acid Ionic Liquids.

Project description:[AAE]X composed of amino acid ester cations is a sort of typically "bio-based" protic ionic liquids (PILs). They possess potential Brønsted acidity due to the active hydrogens on their cations. The Brønsted acidity of [AAE]X PILs in green solvents (water and ethanol) at room temperature was systematically studied. Various frameworks of amino acid ester cations and four anions were investigated in this work from the viewpoint of structure-property relationship. Four different ways were used to study the acidity. Acid dissociation constants (pKa) of [AAE]X determined by the OIM (overlapping indicator method) were from 7.10 to 7.73 in water and from 8.54 to 9.05 in ethanol. The pKa values determined by the PTM (potential titration method) were from 7.12 to 7.82 in water. Their Hammett acidity function (H0) values (0.05 mol·L-1) were about 4.6 in water. In addition, the pKa values obtained by the DFT (proton-transfer reactions) were from 7.11 to 7.83 in water and from 8.54 to 9.34 in ethanol, respectively. The data revealed that the cationic structures of [AAE]X had little effect and the anions had no effect on the acidity of [AAE]X. At the same time, the OIM, PTM, Hammett method and DFT method were reliable for determining the acidic strength of [AAE]X in this study.

| S-EPMC7795477 | biostudies-literature

Synthesis and Physicochemical Properties of Acrylate Anion Based Ionic Liquids.

Project description:Two polymerizable ionic liquids (or monomeric ionic liquids, mILs) namely 1-butyl-3-methylimidazolium and choline acrylates ([C4mim]A and ChA, respectively) were synthesized using the modified Fukumoto method from corresponding chlorides. The chemical structure of the prepared mILs was confirmed with FTIR and NMR study. Investigation of the thermal properties with DSC demonstrates that both mILs have a Tg temperature of about 180 K and a melting point around 310 K. It was shown that the temperature dependence of FTIR confirm the Tg to be below 200. Both mILs exhibited non-Newtonian shear thinning rheological behavior at shear rates >4 s-1. It was shown that [C4mim]A is able to dissolve bacterial cellulose (BC) leading to a decrease in its degree of polymerization and recrystallisation upon regeneration with water; although in the ChA, the crystalline structure and nanofibrous morphology of BC was preserved. It was demonstrated that the thixotropic and rheological properties of cellulose dispersion in ChA at room temperature makes this system a prospective ink for 3D printing with subsequent UV-curing. The 3D printed filaments based on ChA, containing 2 wt% of BC, and 1% of N,N'-methylenebisacrylamide after radical polymerization induced with 1% 2-hydroxy-2-methylpropiophenone, demonstrated Young's modulus 7.1 ± 1.0 MPa with 1.2 ± 0.1 MPa and 40 ± 5% of strength and ultimate elongation, respectively.

| S-EPMC9736722 | biostudies-literature

Effect of Ionic Composition on Physicochemical Properties of Mono-Ether Functional Ionic Liquids.

Project description:Tunable properties prompt the development of different "tailor-made" functional ionic liquids (FILs) for specific tasks. FILs with an ether group are good solvents for many organic compounds and enzymatic reactions. However, ionic composition influences the solubility by affecting the physiochemical properties of these FILs. To address the structure effect, a series of novel FILs with a mono-ether group (ME) based on imidazole were prepared through cationic functionalization and anionic exchange reactions, and characterized by NMR, mass spectroscopy, and Thermogravimetric analysis (TGA). The effect of ionic composition (cationic structure and anions) on density, viscosity, ionic conductivity, electrochemical window, and thermal properties of these ME-FILs were systematically investigated. In general, the viscosity and heat capacity increases with the bigger cationic volume of ME-FILs; in particular, the 2-alkyl substitution of imidazolium enhances the viscosity remarkably, whereas the density and conductivity decrease on the condition of the same [NTf2]- anion; For these ME-FILs with the same cations, the density follows the order of [NTf2]- > [PF6]- > [BF4]-. The viscosity follows the order of [PF6]- > [BF4]- > [NTf2]-. Ion conductivity follows the order of [NTf2]- ? [BF4]- > [PF6]-. It is noted that the dynamic density has a good linear relationship with the temperature, and the slopes are the same for all ME-FILs. Furthermore, these ME-FILs have broad electrochemical windows and glass transition temperatures in addition to a cold crystallization and a melt temperature for ME-FIL7. Therefore, the cationic structure and counter anion affect the physicochemical properties of these ME-FILs together.

| S-EPMC6749295 | biostudies-literature

Exploring the Gas-Permeation Properties of Proton-Conducting Membranes Based on Protic Imidazolium Ionic Liquids: Application in Natural Gas Processing.

Project description:This experimental study explores the potential of supported ionic liquid membranes (SILMs) based on protic imidazolium ionic liquids (ILs) and randomly nanoporous polybenzimidazole (PBI) supports for CH?/N? separation. In particular, three classes of SILMs have been prepared by the infiltration of porous PBI membranes with different protic moieties: 1-H-3-methylimidazolium bis (trifluoromethane sulfonyl)imide; 1-H-3-vinylimidazolium bis(trifluoromethane sulfonyl)imide followed by in situ ultraviolet (UV) polymerization to poly[1-(3H-imidazolium)ethylene] bis(trifluoromethanesulfonyl)imide. The polymerization process has been monitored by Fourier transform infrared (FTIR) spectroscopy and the concentration of the protic entities in the SILMs has been evaluated by thermogravimetric analysis (TGA). Single gas permeability values of N? and CH? at 313 K, 333 K and 363 K were obtained from a series of experiments conducted in a batch gas permeance system. The results obtained were assessed in terms of the preferential cavity formation and favorable solvation of methane in the apolar domains of the protic ionic network. The most attractive behavior exhibited poly[1-(3H-imidazolium)ethylene]bis(trifluoromethanesulfonyl)imide polymeric ionic liquid (PIL) cross-linked with 1% divinylbenzene supported membranes, showing stable performance when increasing the upstream pressure. The CH?/N? permselectivity value of 2.1 with CH? permeability of 156 Barrer at 363 K suggests that the transport mechanism of the as-prepared SILMs is solubility-dominated.

| S-EPMC6161093 | biostudies-literature

Evaluation of Solubility, Physicochemical Properties, and Cytotoxicity of Naproxen-Based Ionic Liquids.

Project description:To solve the problems associated with poorly water-soluble nonsteroidal anti-inflammatory drugs (NSAIDs), naproxen-based ionic liquids (ILs) containing naproxen as an active pharmaceutical ingredient (API) anion were prepared with benzalkonium (tetradecyldimethylbenzyl ammonium), choline, and 1-octyl-3-methylimidazole as the cation. The structures and thermal properties were analyzed. Through the conductivity method, the solubility at 25 and 37 °C and the critical micelle concentration (CMC) at 25 °C were determined in water and ethanol. The octanol-water partition coefficients (K ow) at 25 °C were measured with the shake-flask method. The cytotoxicity was evaluated with the MTT method. The results showed that the conversion of naproxen into the API-ILs increased the API's solubility in water by more than 850 times compared with the original API, and the thermostability was satisfactory with a lower glass transition temperature (t g). Moreover, the variation trends of solubility, hydrophilicity, and K ow were consistent with the different structures of naproxen-based ILs, except for benzalkonium naproxen. The CMC (10-5-10-6 M) in water and ethanol demonstrated that the naproxen-based ILs were surface activite ILs. The IC50 values exhibited the low cytotoxicity of the naproxen-based ILs, which was better than 100 μM. The results provide essential information and a research basis for future topical and transdermal administration and oral administration of naproxen-based ILs.

| S-EPMC9996794 | biostudies-literature

Protic Ionic Liquids for Lignin Extraction-A Lignin Characterization Study.

Project description:Protic ionic liquids (PILs) have been established as effective solvents for the selective extraction and recovery of lignin from lignocellulosic biomass. In this study, we utilize extensive analytical techniques to characterize the PIL-extracted lignins to (1) expand on the physical/chemical structure, and to (2) develop a better understanding of the mechanism behind the lignin dissolution process. The PIL-lignins were characterized using elemental and FT-IR analyses, alongside molecular weight distribution and chemical modeling via MM2. For the more ionic pyrrolidinium acetate ([Pyrr][Ac]), there is an increase in the fragmentation of lignin, resulting in lignin with a smaller average molecular weight and a more uniform dispersity. This lends better understanding to previous findings indicating that higher ionicity in a PIL leads to increased lignin extraction.

| S-EPMC5855650 | biostudies-literature

Physicochemical and structural properties of lidocaine-based ionic liquids with anti-inflammatory anions.

Project description:The purpose of this paper was to examine the density, viscosity and electrical conductivity at different temperatures, as well as the thermal stability and structural properties of previously reported ionic liquids based on active pharmaceutical ingredients. Lidocaine-based ionic liquids, with ibuprofen and salicylate as counterion, were prepared first. Their structures were confirmed by infrared, mass and 1H and 13C nuclear magnetic resonance spectroscopy. The Newtonian behaviour of lidocaine ibuprofenate was confirmed from viscosity measurement results, while it was impossible to determine for lidocaine salicylate. The interactions and structures of the studied ionic liquids were analyzed based on the measured density values, viscosity, electrical conductivity, and calculated values of thermal expansion coefficients and activation energy of viscous flow. From a theoretical aspect, DFT and MD calculations were performed. The obtained descriptors and radial distribution, as well as structural functions, were used to understand the structural organization of the synthesized ionic liquids.

| S-EPMC9051649 | biostudies-literature

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